Literature DB >> 19138149

Design, synthesis, and evaluation of potent, nonpeptidic mimetics of second mitochondria-derived activator of caspases.

Wei Sun1, Zaneta Nikolovska-Coleska, Dongguang Qin, Haiying Sun, Chao-Yie Yang, Longchuang Bai, Su Qiu, You Wang, Dawei Ma, Shaomeng Wang.   

Abstract

A series of new Smac mimetics have been designed, synthesized, and evaluated. The most potent compound 10 binds to XIAP, cIAP-1, and cIAP-2 BIR3 proteins with K(i) of 3.9, 0.37, and 0.25 nM, respectively. Compound 10 antagonizes XIAP in a cell-free functional assay and induces rapid cIAP-1 degradation in cancer cells. Compound 10 inhibits cell growth in the MDA-MB-231 cancer cell line with an IC(50) of 8.9 nM.

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Year:  2009        PMID： 19138149      PMCID： PMC2795317          DOI： 10.1021/jm801101z

Source DB:  PubMed          Journal:  J Med Chem        ISSN： 0022-2623            Impact factor:   7.446


  25 in total

Review 1.  From bench to clinic with apoptosis-based therapeutic agents.

Authors:  D W Nicholson
Journal:  Nature       Date:  2000-10-12       Impact factor: 49.962

Review 2.  IAP proteins: blocking the road to death's door.

Authors:  Guy S Salvesen; Colin S Duckett
Journal:  Nat Rev Mol Cell Biol       Date:  2002-06       Impact factor: 94.444

Review 3.  XIAP: apoptotic brake and promising therapeutic target.

Authors:  M Holcik; H Gibson; R G Korneluk
Journal:  Apoptosis       Date:  2001-08       Impact factor: 4.677

4.  A conserved XIAP-interaction motif in caspase-9 and Smac/DIABLO regulates caspase activity and apoptosis.

Authors:  S M Srinivasula; R Hegde; A Saleh; P Datta; E Shiozaki; J Chai; R A Lee; P D Robbins; T Fernandes-Alnemri; Y Shi; E S Alnemri
Journal:  Nature       Date:  2001-03-01       Impact factor: 49.962

Review 5.  Apoptosis in cancer.

Authors:  S W Lowe; A W Lin
Journal:  Carcinogenesis       Date:  2000-03       Impact factor: 4.944

6.  Structural basis for binding of Smac/DIABLO to the XIAP BIR3 domain.

Authors:  Z Liu; C Sun; E T Olejniczak; R P Meadows; S F Betz; T Oost; J Herrmann; J C Wu; S W Fesik
Journal:  Nature       Date:  2000 Dec 21-28       Impact factor: 49.962

7.  Structural basis of IAP recognition by Smac/DIABLO.

Authors:  G Wu; J Chai; T L Suber; J W Wu; C Du; X Wang; Y Shi
Journal:  Nature       Date:  2000 Dec 21-28       Impact factor: 49.962

8.  Identification of DIABLO, a mammalian protein that promotes apoptosis by binding to and antagonizing IAP proteins.

Authors:  A M Verhagen; P G Ekert; M Pakusch; J Silke; L M Connolly; G E Reid; R L Moritz; R J Simpson; D L Vaux
Journal:  Cell       Date:  2000-07-07       Impact factor: 41.582

9.  SM-164: a novel, bivalent Smac mimetic that induces apoptosis and tumor regression by concurrent removal of the blockade of cIAP-1/2 and XIAP.

Authors:  Jianfeng Lu; Longchuan Bai; Haiying Sun; Zaneta Nikolovska-Coleska; Donna McEachern; Su Qiu; Rebecca S Miller; Han Yi; Sanjeev Shangary; Yi Sun; Jennifer L Meagher; Jeanne A Stuckey; Shaomeng Wang
Journal:  Cancer Res       Date:  2008-11-15       Impact factor: 12.701

10.  Apoptotic crosstalk of TNF receptors: TNF-R2-induces depletion of TRAF2 and IAP proteins and accelerates TNF-R1-dependent activation of caspase-8.

Authors:  Mariola Fotin-Mleczek; Frank Henkler; Dierk Samel; Monica Reichwein; Angelika Hausser; Ingela Parmryd; Peter Scheurich; Johannes A Schmid; Harald Wajant
Journal:  J Cell Sci       Date:  2002-07-01       Impact factor: 5.285
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  9 in total

1.  Dimeric Macrocyclic Antagonists of Inhibitor of Apoptosis Proteins for the Treatment of Cancer.

Authors:  Yong Zhang; Benjamin A Seigal; Nicholas K Terrett; Randy L Talbott; Joseph Fargnoli; Joseph G Naglich; Charu Chaudhry; Shana L Posy; Ragini Vuppugalla; Georgia Cornelius; Ming Lei; Chunlei Wang; Yingru Zhang; Robert J Schmidt; Donna D Wei; Michael M Miller; Martin P Allen; Ling Li; Percy H Carter; Gregory D Vite; Robert M Borzilleri
Journal:  ACS Med Chem Lett       Date:  2015-05-27       Impact factor: 4.345

2.  A potent bivalent Smac mimetic (SM-1200) achieving rapid, complete, and durable tumor regression in mice.

Authors:  Rong Sheng; Haiying Sun; Liu Liu; Jianfeng Lu; Donna McEachern; Guanfeng Wang; Jianfeng Wen; Ping Min; Zhenyun Du; Huirong Lu; Sanmao Kang; Ming Guo; Dajun Yang; Shaomeng Wang
Journal:  J Med Chem       Date:  2013-05-07       Impact factor: 7.446

3.  A potent and orally active antagonist (SM-406/AT-406) of multiple inhibitor of apoptosis proteins (IAPs) in clinical development for cancer treatment.

Authors:  Qian Cai; Haiying Sun; Yuefeng Peng; Jianfeng Lu; Zaneta Nikolovska-Coleska; Donna McEachern; Liu Liu; Su Qiu; Chao-Yie Yang; Rebecca Miller; Han Yi; Tao Zhang; Duxin Sun; Sanmao Kang; Ming Guo; Lance Leopold; Dajun Yang; Shaomeng Wang
Journal:  J Med Chem       Date:  2011-03-28       Impact factor: 7.446

Review 4.  Inhibitor of apoptosis protein family as diagnostic markers and therapeutic targets of colorectal cancer.

Authors:  Koh Miura; Wataru Fujibuchi; Kazuyuki Ishida; Takeshi Naitoh; Hitoshi Ogawa; Toshinori Ando; Nobuki Yazaki; Kazuhiro Watanabe; Sho Haneda; Chikashi Shibata; Iwao Sasaki
Journal:  Surg Today       Date:  2011-01-26       Impact factor: 2.549

5.  Potent bivalent Smac mimetics: effect of the linker on binding to inhibitor of apoptosis proteins (IAPs) and anticancer activity.

Authors:  Haiying Sun; Liu Liu; Jianfeng Lu; Longchuan Bai; Xiaoqin Li; Zaneta Nikolovska-Coleska; Donna McEachern; Chao-Yie Yang; Su Qiu; Han Yi; Duxin Sun; Shaomeng Wang
Journal:  J Med Chem       Date:  2011-04-13       Impact factor: 7.446

6.  Design and synthesis of a simplified inhibitor for XIAP-BIR3 domain.

Authors:  Fernando R Pinacho Crisóstomo; Yongmei Feng; Xuejun Zhu; Kate Welsh; Jing An; John C Reed; Ziwei Huang
Journal:  Bioorg Med Chem Lett       Date:  2009-09-17       Impact factor: 2.823

7.  Importance of ligand reorganization free energy in protein-ligand binding-affinity prediction.

Authors:  Chao-Yie Yang; Haiying Sun; Jianyong Chen; Zaneta Nikolovska-Coleska; Shaomeng Wang
Journal:  J Am Chem Soc       Date:  2009-09-30       Impact factor: 15.419

8.  Design of small-molecule peptidic and nonpeptidic Smac mimetics.

Authors:  Haiying Sun; Zaneta Nikolovska-Coleska; Chao-Yie Yang; Dongguang Qian; Jianfeng Lu; Su Qiu; Longchuan Bai; Yuefeng Peng; Qian Cai; Shaomeng Wang
Journal:  Acc Chem Res       Date:  2008-10       Impact factor: 22.384

9.  Potent and selective small-molecule inhibitors of cIAP1/2 proteins reveal that the binding of Smac mimetics to XIAP BIR3 is not required for their effective induction of cell death in tumor cells.

Authors:  Haiying Sun; Jianfeng Lu; Liu Liu; Chao-Yie Yang; Shaomeng Wang
Journal:  ACS Chem Biol       Date:  2014-02-12       Impact factor: 5.100
  9 in total

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